


Crossing the Line

by Major_Fortune



Series: Widojest Smut [2]
Category: Critical Role (Web Series)
Genre: Dom Caleb Widogast, Dom/sub Play, F/M, Jester is clearly a switch, Light Bondage, Oral Sex, Plot What Plot/Porn Without Plot, Punishment, Shameless Smut, Spanking, Sub Jester, Vaginal Fingering, Vaginal Sex, but Caleb makes such a good Dom too, wizards dont always have to bottom thank you for coming to my TED talk
Language: English
Status: Completed
Published: 2019-07-15
Updated: 2019-07-15
Packaged: 2020-06-28 17:57:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,561
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19817536
Author URL: https://archiveofourown.org/users/Major_Fortune/pseuds/Major_Fortune
Summary: Sometimes Jester is a brat. Sometimes Caleb punishes her for it.AKA Jester and Caleb get into some BDSM shenanigans





	Crossing the Line

**Author's Note:**

> So this is lightly connected to 'Practice Makes Perfect' but you don't have to read that first to enjoy this one (although, as the author of both, I would apreciate it if you did).  
> Also, it was Widowjest week and I only found out half-way so I didn't have time to write anything for it (being a post-grad student will take all your time and your soul...). So here's some smut that has nothing to do with any of the prompts, happy Widowjest week!

Sometimes Jester liked to be a brat.

She had always been naturally mischievous, even as a little girl. It had only gotten worse once the Traveler showed up and filled her head with ideas. But this was different. She had recently started enjoying taking things a bit too far, crossing the line just to see how much she could get away with before Caleb snapped. Before he decided to punish her.

It was all his fault, really. He had gotten her addicted to his punishments, to the mix of pain and pleasure and intoxicating full, undivided attention. And she knew how much he enjoyed her bratty side, even if he didn’t always like the results of her jokes and pranks. He loved that she did it all to get his attention, after being alone for all those years, he like feeling needed, wanted. And, by the Traveler, did she want him!

The last few weeks had been complicated. They had been on the road, on a mission for the Bright Queen and, although Jester enjoyed all the espionage and the monster killing, she also missed spending time alone with Caleb. They had decided to keep their relationship on the down low and, even though she was pretty sure most of the Nein knew there was something between them, they hadn’t even kissed in weeks and Jester was feeling seriously __needy.__

She found him in the library, as always. Essek had recently given him a new book on Dunamancy and he’d been obsessed with it ever since they had returned. Which meant she was being severely neglected.

She tried to get his attention the regular way first. She put on her new Xhorhassian dress, the one with the very low neckline and sat across from him, leaning forward so that her chest was right at eye level.

“Heyyyyy Cay-leb.” She purred, her tail doing languid circles in the air behind her. He didn’t even look up from his book. “Whatcha doing?”

“Transcribing a new spell. I need to focus on this Jester. Can we talk later?”

That was it, that’s when the brat came out. Being ignored was one thing, a terribly boring and annoying thing admittedly, but being dismissed was much, much worse.

“Oh that’s fine, I’ll just be here. Quiet as a mouse. Just doing my thing. You wont even notice me.”

He gave her a curt nod, his eyes never leaving the book. She laid back in her chair and put her feet on the table, her dress rising up to expose her entire thigh, then she kicked her foot out and deliberately pushed a stack of books onto the floor. As they crashed onto the hardwood with a loud series of bangs and Caleb jumped out of his almost trance like state, Jester couldn’t help but giggle.

He looked around, taking in the fallen pile and then her outfit, lingering on the smooth blue skin of her thigh, a hint of a smile playing at the corner of his mouth.

“Ups... I’m just sooo clumsy when I’m bored.” She pouted innocently.

“Are you going to pick them up?” He asked, re-opening his book and grabbing his quill to start transcribing the spell again.

“Hmmm... No, I don’t think I will.”

“Alright, suit yourself.” He went back to his work, the small bit of attention Jester had gathered vanishing.

See, Jester never really intended on taking things as far as she did, the problem was that Caleb was a very patient man and it took quite a bit to get a rise out of him. So she pushed, she crossed the line.

She grabbed one of the books that hadn’t fallen and one of his spare quills and started to draw on the first page. He took a while for Caleb to realize what she was doing and she was pretty sure it wasn’t the noise of the quill on the page, but the absence of her voice that had caught his attention.

“Jester, are you drawing on my books again?” He stopped scrawling, quill still firmly in hand.

“Mayyyyybe...” She added more shading to her drawing, the tip of her tongue sticking out of the side of her mouth.

“Is it a dick?”

“Technically yes, there's one involved, technically...” She giggled again, a hint of a blush creeping up her cheeks.

“I’m afraid to ask but... what is it?”

“Oh, you know, just a portrait... Of Fjord. Naked.” She watched him closely as he ran a hand trough his red hair, irritation making his forehead wrinkle. For a moment, she thought she had him. “Wanna see? I think it’s some of my best work. Very detailed.”

“ _Nein._ I don’t want to interrupt.” He cast his eyes back down, focused once again, but the tension in his face didn’t go away. She was so close, just a little more and she would get her prize.

After a couple of seconds of silence, during which she managed to finish her drawing (it really was one of her best, very accurate from what she remembered from that time they had all gone to a bathhouse), she tried again. She stretched her leg over the desk, as far as it would go and, with just the tip of her toe, pushed Caleb’s inkwell. The ink started to spill slowly, inching closer to his parchment. At first he didn’t even notice but when it started to soak trough his intricate designs, he pushed his chair away from the desk and jumped up.

“Okay, that’s quite enough.”

He stalked up to her and she waited, her body tense, readying itself for his touch. He grabbed her by the arm and pulled her to her feet, his grip firm but not painful. He then pushed her against the desk, pressing his body against hers, one leg between hers.

They were both aware that Jester was much stronger than him and that she could reverse their roles at any time, if she wanted to. But their game wasn’t about strength, it was about trust, about giving and taking.

“You’re impossible today, Jester.” He looked her in the eye, his gaze so intense it burned trough her.

“What are you gonna do about it?” She asked, trying to sound sexy but being betrayed by the slight squeak in her voice.

He ran a hand up her chest, making her shiver, and grabbed her neck, pushing her head up with the tip of his finger. “I think you need to be punished. My room, now.”

She grinned in victory. “Yes, Sir.”

Satisfied, he stepped back, letting her go. But his eyes stayed on her as she walked towards his room, ravaging her body from afar.

She walked in, almost giddy with excitement and went trough her usual routine, taking off her armor and her dress until all that was left was her silky shift, then she waited, sitting at the bottom of his bed. He came soon after, walking slowly, gracefully, like a cat, and took his time taking off his coat and rolling up his sleeves. He only looked at her when he was done.

“Come here.” He ordered, his voice low, his accent somewhat thicker than usual.

She obediently walked over and he turned her around, using his scarf to bind her arms behind her back, the knots sturdy, efficient.

“Do you know why I have to do this?” He whispered in her ear, biting her earlobe hard enough to make her gasp.

“Because I misbehaved.” She leaned back against him, feeling his body heat even trough his clothes. She couldn’t help but giggle a little, half excited, half nervous. “Because I was bad.”

“ _Ja._ ” He sat down at the edge of the bed and patted his lap. “And now I need to make sure you learn your lesson. Lay down.”

Caleb was so much better than her at playing his part, when he got in this head space he was all passion and intensity. Not the Caleb that stuttered and threw up when he was nervous but the battle mage that would stand up to pirates and empresses, the one that could burn the world down with a flick of his wrist.

What Jester lacked in discipline, however, she made up for in enthusiasm.

She laid on his lap, belly down, ass up, her legs apart to help her balance. She already knew what was coming, her body tingled with anticipation. He lifted the hem of her shift up to her waist, exposing her to the cold air. She was so glad she hadn’t put on any panties.

He grabbed her ass, massaging it roughly, warming her up for what was coming next.

“Do you remember your safe word, _Liebling_?” She nodded. “ _Gut._ I want you to count. I’m thinking... 20 today?” He lifted his hand and brought it back down on her backside with a resounding crack, the slap immediately turning her skin a soft violet and making her moan.

“One.”

He spanked her again. “In Zemnian. Start again.”

“But...I don’t...” He gave her an assertive look, his hand raised again and she felt her legs go weak. “Yes, Sir.”

 _Crack._

“ _Ein_...” He had taught her some Zemnian just for this. He knew she was not great at it but that was part of the fun.

 _Crack._

“ _Zwei. _..”_ Crack _. “_ Vier _...”__

“You forgot three. Start over.”

She whined a little but did as she was told. By the time they got to five her ass felt like it was on pins and needles, even when he wasn’t touching it. She knew she would be bruised in the morning and relished at the thought.

“ _Sechs _...__ Oh fuuuck! _ _”__ She moaned as the seventh slap landed, her brain too fogged by pain and pleasure to focus on the numbers.

“You missed one. Start over.” She struggled to answer and he took the time to run his hands over her sore skin, letting his fingers slip between her legs. “Gods, you’re so wet already. Are you enjoying your punishment?”

“Yes, Sir. Thank you, Sir.”

He slipped two fingers inside her and she whimpered, struggling to keep her legs steady. He started moving his fingers, even as he smacked her again. “I told you to start over. I’ll tell you what, if you make it to ten without messing up, I’ll stop.”

She didn’t really want him to stop but she obeyed, counting his every strike, even when she stumbled trough her words and moaned so loudly she was sure everyone in the house could hear.

“Caleb, Sir... I’m so close, I think I’m gonna...” She mumbled after the ninth slap, her face buried in the mattress. He took his fingers away and she groaned with disappointment, tears of frustration making her eyes sting.

“No, you’re not. You haven’t earned it yet. Now finish the counting.” He slapped her one last time and she said her final number.

“Good girl.” He whispered, running his hand over her bruised skin gently. Her body trembled all over, she loved it when he called her that. “You look so pretty like this, _Liebling _.__ It almost makes me forget what you did. Almost.”

“Thank you, Sir. Do I get to cum now?” She pleaded.

He chuckled. “Not yet. You still haven’t apologized for what you did. Kneel for me, Jester.”

She got off his lap, her legs were shaking wildly but it didn’t matter because she immediately fell to her knees in front of him. He took her face in his hand, lifting her chin up so she could look at him pleadingly, adoringly.

“I’m so sorry for being a brat, Sir. I’m sorry for messing with your books and your spells.”

He ran his finger over her bottom lip, opening her mouth. She took it in eagerly, sucking and lapping at it. His skin tasted like ink and paper and _her_. She was so turned on she could cry.

“And how are you going to make it up to me?” He asked, taking his fingers away, which only made her more frustrated. “You ruined precious paper and ink, you know?”

“I’ll make up for it, Sir. I promise.”

“How? I want to hear your pretty little mouth say it.” He smirked dangerously, a shadow of the evil archmage he had almost become poking trough his calm facade.

“I’m going to suck your dick, Sir.” She said with feigning innocence. Caleb’s hands gripped the sheets as a shiver of pleasure ran trough him. She settled between his legs and he started to unlace his trousers. “May I?” She asked.

He nodded. She knew Caleb was usually good at hiding his emotions but his body never lied, he was painfully hard, his head beaded with pre-cum. In one long lick, she tasted him from bottom to top, cleaning up every last bit of liquid. Caleb let out a strangled moan, and grabbed her hair, demanding more. She took him into her mouth, he tongue flat against the veined underside of his shaft. He tangled his fingers deeper in her hair, grabbed one of her horns with his other hand and started to guide her, in and out. She worked him over fast and hard, her mouth wet and sloppy, her tongue exploring every inch of him as she sucked.

His breath became increasingly faster and his hold on her tightened, as he pushed himself deeper into her until her eyes started to water. She ran her tongue around the head of his dick and he let out a string of curses, both in Common and Zemnian, before gently pushing her away, her mouth letting go with a wet _pop _.__

“Nooo!” She whined. “Let me finish! I wanna be a good girl for you, Sir.” She tried reaching for him, struggling against the scarf binding her wrists, inadvertedly making it tighter.

“Always so eager, my Jester...” He got up and walked behind her to release her wrists. As he untied the knots and blood started to flow freely to the tips of her finger again, both her hands began to tingle uncomfortably. “You’ve already proven to me how good you are, _Liebling._ I’ll let you continue, if you want... but was thinking about making you cum now.”

She bit her lip, looking at him over her shoulder, indecision making her tongue-tied. This situation was not unusual for them. Caleb liked to be in control, Jester knew it was in part due to all the years he wasn’t in control of himself, first being under Ikithon’s influence, then losing a hold of his own mind. They rarely talked about it, it hurt him too much and she hated seeing the light in his eyes dim. But she knew their little games helped, letting him be in control made him feel safe, confident, trusted. And giving herself to him made her feel loved, worshipped.

But she knew that deep down Caleb was a giver, even when in charge, he only cared about how he made her feel. If she didn’t push him, she knew he would always put her needs above his, masochistically ignoring himself completely, if possible.

She wanted him to enjoy himself first, for once, specially after crossing the line so badly to get his attention. But she was also painfully in need of his touch. Deep down, she was a taker.

“Decide, Jester.” Hi whispered in her ear.

“Can we both cum?”

He chuckled and kissed her shoulder tenderly, signaling to her that the punishment was over. This was her reward, it was after-care. He was no longer Sir, just Caleb, her Caleb. Jester wanted to say this was her favourite part, but she honestly loved it all.

“What do you have in mind?”

“Fuck me, please! On the bed.”

He helped her up and she practically jumped on the mattress, settling in among the pillows and waiting impatiently, her tail swiveling in the air, while he took the rest of his clothes off. When he came to her she couldn’t help herself, after being denied the right to touch him, she ran her hands over his shoulders, down his chest, finally tangling them in the silky strands of his hair. He kissed her slowly and she felt like a a dying man in a desert, finally finding water. She wanted him with a burning intensity that couldn’t wait, all of him.

“Now, please! I’ll go insane if you make me wait any longer.” She wrapped her legs around his waist, opening for him and pulling him closer.

“As you wish, _Liebling. _”__ He entered her carefully, letting her get used to his length and she gasped, her tail gripping his leg like a vice. “This is your reward _ _.__ Do you want me to go slow? _ _”__

She nodded. He always asked her the same question, ever since her first time, and she always said yes, but they never ended up following trough. They were both over eager, all fire and want and even though they could start as slowly and romantically as they promised, they always ended up panting and sweating, covered in bite marks and scratches. 

“You’re the best reward I could ask for, Cayleb.” She moaned and he moved inside her, his thrusts picking up speed as she tightened her grip around him, her nails digging into his back.

After all the teasing and waiting Jester knew she wouldn’t last long and when she saw Caleb bite his lip, his icy blue stare locked on hers, she knew he was close too. He gripped the headboard for leverage, his rhythm frantic, but his other cupped her cheek gently, his fingers making slow circles on her skin. She could see his eyes were clouded and his mouth trembled like he was holding back words that fought to get out. They had never put their relationship into words, never gave it a name or talked about being exclusive. There was a war out there and their line of work was a dangerous one, there was no point in making promises they probably couldn’t keep. But, even though they had never said it, Jester knew she loved him and he loved her, even if he couldn’t allow himself to voice his feelings. 

“ _Scheisse!_ ” He said instead, as he came inside her. His final trust pushed her over the edge and she came too, screaming his name.

They laid in each-others arms for the longest time, shaking as they rode out the waves of pleasure. When it was over, he got up and grabbed a clean rag and a basin full of fresh water. With gentle, precise motions, he started cleaning every inch of her body, worshiping all of her skin like she was his Goddess. He cared for her, that’s how he said ‘I love you’.

“Was it worth it? Making all that mess?” He asked, passing the rag slowly between the swells of her breasts.

“Absolutely. I would destroy all your books for more of this.” She said, capturing his lips with hers. That’s how she said ‘I love you too’.

He laughed. “You know you don’t need to. All you have to do is ask.”

“Yeeees, but this way it’s more fun.”

He dragged the cloth down her arms, stopping when he saw the bruised skin on her wrists. He closed his eyes for a second, then kissed the tender skin.

“Fuck! I’m sorry, Jester! You should have told me it was too tight.” He eyed her with a mixture of fear and worry. Like this one mistake would be all it took to make her realize she should never have let him touch her. Which was ridiculous, but not unusual for Caleb. He always hesitated, like he was afraid of breaking her, like his touch would set her on fire. “You should have used your safe word.”

“But I didn’t want you to stop.” She knelt on the bed and put her arms around his neck, kissing his forehead and his cheeks, one at a time, trying to kiss his worries away. Then she said a quick prayer of healing and watched her bruises fade, her wrists going back to their usual pale blue color. “It’s not a big deal, see?”

“But..” He stated to argue, putting the rag and the basin down. Jester shushed him by using her superior strength to pull him back on the bed.

“No butts... except maybe mine, but that’s still a little sore.” She stuck her tongue out and he laughed, all tension gone from his face. “Oh, and by the way, I think we need to change our safe word.”

“Yeah?” He raised one auburn eyebrow. “You don’t like it?”

“Not reeeeally, it’s kind of awkward. Why did you pick _Beauregard_ , anyway?”

“It was the biggest turnoff I could think of.” He shrugged and Jester punched his shoulder playfully, very aware of how fragile he was in comparison to her.

“Cayyyy-leb! If she ever finds out we’re using her name in bed I don’t know if she would immediately die of embarrassment or kill you first.”

“Both. She would probably find a way back from the grave to kill me. But that, as you said, makes it more fun.” She curled up against him, her head laying on his chest.

“I think I’m rubbing off on you. I’m a terrible influence.”

“No Lavorre, you’re the best.”


End file.
